Portland, Maine: a getaway by land and sea

Spring Point Ledge Lighthouse with Portland Head Lighthouse in the background

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Fish market, Portland, Maine

Maine is known as as Vacationland with good reason. The Pine Tree State is known for lobsters, lighthouses, camping, sea breezes, a rugged rocky coast and its rustic charm.

Portland, its largest metropolitan area, is also a place to experience a comfortable and casual sophistication. It is a city with fine art, innovative cuisine, live performances, historical attractions and upscale accommodations.

The Portland by Land and by Sea package is a four day, three night getaway that includes a one night stay on the mainland followed by two nights on an island in the harbor. There is time to explore the attractions of the city followed by a relaxing stay at a private island enclave in a unique historic setting.

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The Portland Harbor Hotel, Portland, Maine

It begins at the Portland Harbor Hotel, the city’s only AAA Four Diamond Hotel. It is in the restored historic Old Port district, just a block from one of America’soldest working seaports.

After the city stay, hotel guests are taken by town car for a cruise on Casco Bay to Great Diamond Island and a car-free experience. Golf carts await for the ride to the Inn at Diamond Cove.

The Portland Harbor Hotel

The Portland Harbor Hotel was renovated in 2017 with distinctive nautical design elements to reflect Portland’s heritage as a New England port city. It begins with the lobby’skinetic sculpture of fish that appear to swim with the breeze.

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detail of the wood flooring, Portland Harbor Hotel, Portland, Maine

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Kinetic fish sculpture, Portland Harbor Hotel, Portland, Maine

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lobby, Portland Harbor Hotel, Portland, Maine

Guest rooms and public spaces feature art by well-known Maine artists and artisans, from the Thomas Moser custom furniture to the framed nautical flags above the beds that were hand crafted by Angela Adams. Monochromatic maritime photography by Jim Dugan hangs in public spaces of the hotel.

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guest room, Portland Harbor Hotel, Portland, Maine

Should you want a refreshing drink, there is a pantry on each floor. A faucet produces both plain and sparkling water and a variety of complimentary beverages — including Starbucks coffee. hot chocolate, and Tazo chai latte –may be selected from a large touchscreen.

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BlueFin Restaurant, Portland Harbor Hotel, Portland, Maine

There is casual, relaxed fine dining at the hotel’s BlueFin North Atlantic Seafood Restaurant. When the weather permits, dining can be al fresco in the outdoor garden courtyard.The fire pit is a popular spot to relax with cocktails or a glass of wine.

Maine native and Executive Chef Tim Labonte has created a menu inspired by fresh locally-caught seafood and ingredients from local dairies and farms. The traditional and innovative dishes change seasonally.

Signature items include Maine crab cakes and a lobster roll popover with lemon-thyme dressing. Halibut with kelp noodles, plankton and pulverized uni (sea urchin) was recently featured in a tasting menu.

GQ and others have named Portland one of the coolest small cities in America. Unique specialty shops and restaurants line Old Port’s Commercial Street.

Together with the Uptown wine and jazz bars, it is the place to find live music and other nightlife. The Arts District is centered on Congress Street, a culture center with museums, galleries, and historic sites like the Portland Observatory.

Portland is a place to enjoy ballet, opera, symphony orchestra, and theater. Museum houses reflect Colonial times through Victorian and Industrial Age opulence. Visit early in the month for a First Friday Art Walk.

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Old Port, Portland, Maine

From the freshest seafood to the most innovative creations Portland is known for its culinary scene. Bon Appétit named Portland the foodiest small town in America and there are tours to prove it.

Maine became the first dry state in 1851, well before Prohibition began in 1920. Speakeasy-style bars still exist here.

Portland is also known for the craft breweries, wineries and distilleries with tasting rooms and tours.

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Geary’s tasting room, Portland, Maine

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Geary’s brewery, Portland, Maine

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Ned Wight, New England Distilling

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awards medals, New England Distilling

Companies like the Brew Bus offer a variety of tours to places like D. L. Geary’s, the first post-Prohibition craft brewery east of the Rockies, and Ned Wight’s New England Distilling, where there’s a family history of producing rye whiskey, bourbon, gin, and rum that goes back to Wight’s great-great-great-grandfather, John Jacob Wight, during the 1850’s.

Points of Interest

Enjoy a range of American, European and contemporary works at Portland Museum of Art. Reserve in advance for an exclusive tour of Winslow Homer’s home and studio on Prout’s Neck.

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Winslow Homer studio, Prouts Neck,Scarborough, Maine

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McLellan-Sweat-House, part of the Portland Museum of Art Complex

Climb the 86’ tall Portland Observatory, America’s last standing maritime signal tower, for a bird’s eye view of the busy harbor. It was built in 1807 by Captain Lemuel Moody, who hoisted signal flags to alert subscribing ship owners and merchants that their ships and cargo were approaching.

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Portland Observatory, Portland, Maine

Henry Wadsworth Longfellow House & Garden, at the Maine Historical Society, is the 19th century poet’s childhood home. It was built 1785-1786 by his grandfather, General Peleg Wadsworth, and has been restored to the 1850s. Family furnishings and memorabilia are original.

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Wadsworth-Longfellow House, Portland, Maine

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Victoria Mansion, Portland, Maine

Victoria Mansion is one of America’s best examples of Italian Villa style. It was built between 1858 and 1860 as a summer house for Maine-born Ruggles Sylvester Morse, who made a fortune in luxury hotels in New Orleans, and wife Olive. It was purchased by dry goods merchant J. R. Libby and is also known as the Morse-Libby Mansion. Over 90% of the furnishings are original.

Tate House (built in 1755), was the home of Captain George Tate, Maine’s last agent to supply he British Navy with Maine white pines for masts. It is the only pre-Revolutionary home in Greater Portland open to the public. There are period furnishings and herb gardens.

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Portland Head Lighthouse, Cape Elizabeth, Maine

There are six lighthouses within a twenty minute drive of the city. The most photographed, Portland Head Light in Cape Elizabeth, is the oldest lighthouse in Maine It was authorized by President George Washington. The lighthouse keeper’s quarters is now a museum that also includes the history of the adjacent Fort Williams, a military outpost for coastal defense.

Inn at Diamond Cove: an island getaway

A 30 minute cruise from the mainland on Casco Bay brings guests to Great Diamond Island. The tranquility and natural beauty of the island is accessible to residents and those who stay at the stylish Inn at Diamond Cove or dine at Diamond’s Edge Restaurant.

Cruise in the salt air past lighthouses, forts, lobster boats, and seabirds. You might even spot a bald eagle.

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bald eagle, Portland, Maine

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osprey nest, Casco Bay, Portland, Maine

A driver awaits with a golf cart to escort you to the inn. Whether for a romantic getaway, an immersion in history, or as a family or group getaway, it feels worlds away.

A charter boat company offers service to the inn by the J.S. Kennedy, a 50 ft. decommissioned Navy UB85, or “Utility Boat,” from Boston built in 1985. It was named for Joseph S. Kennedy, who completed three different tours of duty with the U.S. Navy in both World War I and World War II.

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UB85 boat, Great Diamond Island, Portland, Maine

The island can also be accessed by ferry, water taxi or private boat. There is a marina with deep water slips.

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Casco Bay Islands Ferry at Great Diamond Island, Portland, Maine

In tribute to the inn’s fire and rebuilding, a stained glass phoenix looms over the inn’s lobby fireplace. The phoenix is the emblem of the city of Portland, which was devastated four times by fire. Portland’s motto is “I will rise again.”

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The Inn at Diamond Cove, Great Diamond Island, Portland, Maine

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lobby, Inn at Diamond Cove, Great Diamond Island

The Inn at Diamond Cove has 44 well appointed guest rooms and suites. All suites have a fireplace, kitchen, dining area, parlor, and a wide wooden porch with a comfortable seating area. Suites can be connected to adjacent guest rooms to accommodate families or other groups.

There is an outdoor pool with a cabana. Guests can also enjoy the walking trails, secluded beaches, complimentary bicycles, tennis, and yoga. A fire pit adds warmth to a chilly night.

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pool, Inn at Diamond Cove, Great Diamond Island

You can even test your skill at the hand operated bowling alley.

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bowling, Inn at Diamond Cove, Great Diamond Island, Portland, Maine

This unique inn is in a meticulously restored army barracks that was part of theformer Fort McKinley. This military base was built between 1891 and 1907 for coastal defense during the Spanish-American War. It was also used during World War 1 and World War 2,. It was retired from active duty in 1945, and passed to U. S. Navy in 1954.

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private residences at the former Fort McKinley, Great Diamond Island

Before Diamond Cove was an army base it was popular as a retreat for writers and artists. Harriet Beecher Stowe and Henry Wadsworth Longfellow are among those who visited.

The Navy sold property to private investor in 1961. The fort was eventually sold to thedeveloper who built the inn. It was gutted by fire just before completion in 2013, and rebuilt, thanks to historic tax credits, and opened in 2015. Itis on the National Register of Historic Places and a member of the Historic Hotels of America.

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Moon Garden, Great Diamond Island, Portland, Maine

Staff members will point out areas of interest to guests who request a golf cart tour. Adirondack chairs mark scenic spots like Moon Garden, site of the former Engineer’s Wharf and a place for watching for wildlife or sunsets over Casco Bay.

Pleasant Cove Beach is known as Sea Glass Beach for the abundance of fragments that wash up.

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Adirondack chairs overlooking Sea Glass Beach, Great Diamond Island

This is a place to relax and enjoy the serenity away from it all. Savor a leisurely breakfast, perhaps a lobster omelet, and dinner at the inn’s restaurant, where lobster rolls, crab cakes and an oversized pork chop with apple bourbon bacon chutney are top choices. Meals are served in the lobby area or al fresco on the patio, weather permitting.

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lobster omelet, Inn at Diamond Cove, Great Diamond Island

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Moon Garden Punch, one of the specialty drinks at the Inn at Diamond Cove, Great Diamond Island, Portland, Maine

Another night, dinner is in the waterfront Diamond’s Edge Restaurant, their free-standing restaurant in the former Quartermaster’s storehouse. It is open for lunch or dinner Tuesday-Sunday in the summer and for Sunday Brunch.

Other favorites are the black garlic & blue cheese crusted filet mignon and the bouillabaisse, which overflows with the fresh catch, mussels, shrimp, cod, salmon, scallops, and lobster, as well, if you like. Or add a side of lobster garlic smashed potatoes. If the weather allows, dinner is also served on the deck or on the lawn.

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Bouillabaisse, Diamond’s Edge Restaurant & Marina

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Special of the day, halibut, at Diamond’s Edge Restaurant

To learn more about the area’s history, visit the Ft. McKinley Museum, generally open June-September 11-2. It is staffed by volunteers from the Diamond Cove Homeowner’s Association.

The Portland by Land and by Sea Package is offered until Friday, September 21st and is subject to availability. Rates start at $1,375. Contact the Inn at Diamond Cove or the Portland Harbor Hotel for details.

Portland is a 90 minute drive from Boston. It is 5 minutes from the Downeaster Rail Terminal, and 10 minutes from Portland Jetport. Valet parking at the Portland Harbor Hotel is included throughout the stay.